US6121457AExpiredUtility
Compositions and methods using novel substituted imidazolium lipids
Est. expiryNov 14, 2017(expired)· nominal 20-yr term from priority
C07D 233/22C07D 233/24
61
PatentIndex Score
8
Cited by
7
References
22
Claims
Abstract
Compounds of the formula: ##STR1## are provided, in which R 1 and R 2 each independently represent a C 8 -C 24 saturated or unsaturated hydrocarbon chain, which is optionally interrupted by from 1 to 3 heteroatom moieties, such as --O--, --S--, --NH-- and --NR--. The symbol X represents --CH 2 --, --O--, --S--, --NH-- or --NR--. The R group for each of the --NR-- moieties represents an alkyl group having from 1 to 4 carbon atoms. Finally, the subscript n represents the integer 1 or 2, and A - represents an anion, preferably chloride or citrate.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1. A compound having the formula: ##STR13## wherein R 1 and R 2 each independently represent a C 8 -C 24 saturated or unsaturated hydrocarbon chain, uninterrupted or interrupted by from 1 to 3 heteroatom moieties selected from the group consisting of --O--, --S--, --NH-- and --NR--; X represents a member selected from the group consisting of --CH 2 --, --O--, --S--, --NH-- and --NR--; wherein R is a lower alkyl group having from 1 to 4 carbon atoms; n is an integer of from 1 to 2; and A - is an anion.
2. A compound of claim 1, wherein R 1 and R 2 each independently represent a C 8 -C 24 saturated or unsaturated hydrocarbon chain.
3. A compound of claim 1, wherein R 1 and R 2 each independently represent a C 12 -C 20 saturated hydrocarbon chain.
4. A compound of claim 1, wherein R 1 and R 2 each independently represent a C 12 -C 20 unsaturated hydrocarbon chain.
5. A compound of claim 1, wherein n is 1.
6. A compound of claim 1, wherein R 1 and R 2 each independently represent a C 12 -C 16 unsaturated hydrocarbon chain, X is --O--, and n is 1.
7. A compound of claim 1, wherein R 1 represents a C 18 -unsaturated hydrocarbon chain, R 2 represents a C 17 unsaturated hydrocarbon chain, X is --O--, and n is 1.
8. A compound of claim 7, wherein R 1 and R 2 each contain a single double bond in the cis orientation.
9. A compound according to claim 1 having the formula: ##STR14##10.
10. A compound according to claim 1 having the formula:
11. A lipid vesicle composition containing a lipid of the formula: wherein R 1 and R 2 each independently represent a C 8 -C 24 saturated or unsaturated hydrocarbon chain, uninterrupted or interrupted by from 1 to 3 heteroatom moieties selected from the group consisting of --O--, --S--, --NH-- and --NR--; X represents a member selected from the group consisting of --CH 2 --, --O--, --S--, --NH-- and --NR--; wherein R is a lower alkyl group having from 1 to 4 carbon atoms; n is an integer of from 1 to 2; and A - is an anion.
12. A composition of claim 11, wherein R 1 and R 2 each independently represent a C 8 -C 24 saturated or unsaturated hydrocarbon chain.
13. A composition of claim 11, wherein R 1 and R 2 each independently represent a C 12 -C 20 saturated hydrocarbon chain.
14. A composition of claim 11, wherein R 1 and R 2 each independently represent a C 12 -C 20 unsaturated hydrocarbon chain.
15. A composition of claim 11, wherein n is 1.
16. A composition of claim 11, wherein R 1 and R 2 each independently represent a C 12 -C 16 unsaturated hydrocarbon chain, X is --O--, and n is 1.
17. A composition of claim 11, wherein R 1 represents a C 18 -unsaturated hydrocarbon chain, R 2 represents a C 17 unsaturated hydrocarbon chain, X is --O--, and n is 1.
18. A composition of claim 17, wherein R 1 and R 2 each contain a single double bond in the cis orientation.
19. A composition of claim 11, further comprising cholesterol.
20. A composition of claim 11, further comprising dilauroylphosphatidylethanolamine.
21. A composition of claim 11 which is in the form of unilamellar vesicles.
22. A lipid-nucleic acid composition comprising a nucleic acid and a compound of formula: ##STR15## wherein R 1 and R 2 each independently represent a C 8 -C 24 saturated or unsaturated hydrocarbon chain, uninterrupted or interrupted by from 1 to 3 heteroatom moieties selected from the group consisting of --O--, --S--, --NH-- and --NR--; X represents a member selected from the group consisting of --CH 2 --, --O--, --S--, --NH-- and --NR--; wherein R is a lower alkyl group having from 1 to 4 carbon atoms; n is an integer of from 1 to 2; and A - is an anion.Cited by (0)
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